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Swimming pool
Wireless Internet
Air conditioning
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
Sea view
Safe
Dishwasher
Children's pool
Shared outdoor pool (heated)
Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Pool or snooker table
Ceiling Fans
Clothes dryer
Games room
Table tennis
Cribs
Swing set or jungle gym
Fax machine
Linen provided
Iron
Hair dryer
Stove
Fridge
Freezer
Microwave
Towels provided
Video player
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Boat available
Housekeeping Included

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Pets allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible

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Skiing – property near ski resort
Walking trips
Tennis in town
Nightlife

Water sports
Horse riding
Fishing
Golf course on site or within 15 min walk
Golf within 30mins drive
Waterfront

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627 Houses in Osprey with pools

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LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$161

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms
3 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$655

Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key

Osprey condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$161

Great rentals within 20 miles that match your search

Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated - Siesta Sky

Siesta Key condo

1 bedroom
1 bathroom

sleeps 2

Match: Swimming pool

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Price per night from

$333

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

2 bedrooms
1 bathroom

sleeps 3

Match: Swimming pool

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Price per night from

$574

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$213

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$345

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$272

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

6 bedrooms
5 bathrooms

sleeps 14

Match: Swimming pool

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Price per night from

$1,001

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$115

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

3 bedrooms
2 bathrooms

sleeps 5

Match: Swimming pool

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Price per night from

$155

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Swimming pool

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Price per night from

$402

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

2 bedrooms
4 bathrooms

sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$431

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key studio

Studio
1 bathroom

sleeps 3

“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$194

Manasota Beach Vacation Rental

Englewood house

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$270

Beach front condo in Longboat Key

Longboat Key condo

1 bedroom
1 bathroom

sleeps 4

Match: Swimming pool

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Price per night from

$431

Beachfront Getaway in Siesta Key

Siesta Key townhouse

1 bedroom
1 bathroom

sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

Match: Swimming pool

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Price per night from

$224

Quiet pool home with lake view, close to beaches

Venice house

2 bedrooms
2 bathrooms

sleeps 4

Match: Swimming pool

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Price per night from

$230

Tara Golf & Country Club Condo

Bradenton condo

2 bedrooms
2 bathrooms

sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

Match: Swimming pool

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Price per night from

$144

Brand new villa with heated pool for swimmers

Venice house

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$190

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & Save 10% to 25% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$285

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

3 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$128

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 4

Match: Swimming pool

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Price per night from

$161

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

Match: Swimming pool

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Price per night from

$201

Luxury Sarasota Golf Home

Sarasota house

4 bedrooms
4 bathrooms

sleeps 8

Match: Swimming pool

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Price per night from

$369

Enjoy our pool and prime location for beach, downtown and bike trail.

Venice house

2 bedrooms
2 bathrooms

sleeps 4

Match: Swimming pool

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Price per night from

$150

Shorewalk waterfront Condo Bradenton

Bradenton condo

2 bedrooms
2 bathrooms

sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

Match: Swimming pool

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Price per night from

$96

Ground Level 2 Bedroom Beach Themed Condo

Venice condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$230

Little Palms Villa. A lakeside home with style.

Bradenton villa

3 bedrooms
2 bathrooms

sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

Match: Swimming pool

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Price per night from

$195

Luxury Beach Cotttage

Sarasota cottage

1 bedroom
1 bathroom

sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

Match: Swimming pool

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Price per night from

$533

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

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Price per night from

$345

Beachfront Condo Siesta Key

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

Match: Swimming pool

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Price per night from

$454

Super clean vacation Villa with Pool

North Port house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$138

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

2 bedrooms
1 bathroom

sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

Match: Swimming pool

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Price per night from

$259